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Check prices for these dates

Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov
In one month
5 Dec - 7 Dec
In two months
2 Jan - 4 Jan

Browse Select Southwest Side B&B

Private kitchen
The Sono Chicago

The Sono Chicago

3.5 star property
Near North Side
10.0 out of 10, Exceptional, (479)
"Great location and hospitality! "
United States
Teresa
The price is 3.757.068 ₫
4.410.608 ₫ total
includes taxes & fees
13 Nov - 14 Nov
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (187)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is 5.768.204 ₫
6.511.725 ₫ total
includes taxes & fees
16 Nov - 17 Nov
The Publishing House B&B
Free WiFi, bed sheets
Dorothy's

Dorothy's

3.0 star property
Lakeview
8.4 out of 10, Very good, (92)
"Halsted is a nice neibourhood. We liked the secondhand shops."
United States
Lisa
The price is 994.518 ₫
2.088.315 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Dorothy's
Exterior
The Villa Toscana

The Villa Toscana

2.5 star property
Lakeview
7.8 out of 10, Good, (616)
"We "
United States
Brian
The price is 1.136.592 ₫
2.386.646 ₫ total
includes taxes & fees
10 Nov - 11 Nov
The Villa Toscana
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property
Edgewater
9.0 out of 10, Wonderful, (490)
"I loved it was so close to busy Chicago but in the quiet subarbs where it was nice and quiet and felt very safe.The rooms were excellent and well equipped and the kitchen was full of snacks to eat when you wanted and a great selection of drinks. If I ever came to Chicago I would stay here again also the hosts were fantastic "
United Kingdom
Mark
The price is 2.995.394 ₫
4.962.856 ₫ total
includes taxes & fees
13 Nov - 14 Nov
House 5863 - Chicago Bed and Breakfast
Lobby sitting area
Villa D' Citta

Villa D' Citta

3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (110)
"Would stay again anytime!!"
United States
Dominic
The price is 5.415.914 ₫
6.357.812 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Villa D' Citta
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (119)
"Beautiful home, welcoming host."
United States
scott
The price is 6.077.610 ₫
6.744.832 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Harvey House Bed & Breakfast
Front of property
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 star property
Bucktown
9.8 out of 10, Exceptional, (381)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is 4.432.446 ₫
5.003.636 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Ray's Bucktown B&B
Property entrance
Wicker Park Inn

Wicker Park Inn

3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"My husband and I loved our stay. The room was beautiful, clean, and comfortable. Being able to stay in a neighborhood inn made our trip to Chicago memorable. We went to the Wicker Park Farmer's Market, ate at local restaurants, hung out at local bars, met cool people, and just enjoyed being part of the city. "
United States
Melissa
Wicker Park Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southwest Side Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"The rooms are smaller than usual, but super clean and convenient. They're nice for a night or 2. A couple issues...there is no plug near the bed, so if you have something like a CPAP machine, bring an extension cord. Also, the bathroom has no fan. Be prepared to leave if you're partner has to relieve themselves. You'll hear EVERYTHING! But overall it was close to a so many dining and shopping options."
Dave 1-night trip
Posted 15 hours ago
citizenM Chicago Downtown

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Southwest Side B&B information

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